


Wine Ain't That Bad

by helvetesfonster



Category: Supernatural
Genre: Alternate Universe - No Powers, Brief mention of cancer, Dean Winchester-centric, Fluff, I swear to God, Implied Sexual Content, It's All Very Sweet, M/M, Rich Castiel (Supernatural), Rock Star Dean Winchester, Sexual Tension, Wine, brief explicit sexual content, brief mention of a car crash, cas is italian, lots of fucking wine, may be ooc bc i'm not super familiar with them, side destiel, this is a romcom
Language: English
Status: Completed
Published: 2020-11-01
Updated: 2020-11-01
Packaged: 2021-03-09 04:01:00
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 20,016
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27328468
Author URL: https://archiveofourown.org/users/helvetesfonster/pseuds/helvetesfonster
Summary: It was hard to let go of everything. Working his ass off to achieve his dreams was the only thing Dean knew how to do. He didn’t finish school, which meant going to college wasn’t an option. Music was the only thing he ever had in mind. And now he was supposed to let go of it? For an entire month?or, the one where Dean didn't expect to fall for an Italian.(birthday fic for a dear friend <3)
Relationships: Castiel/Dean Winchester
Comments: 1
Kudos: 39





	Wine Ain't That Bad

**Author's Note:**

  * For [Cardinal_Rat_Man](https://archiveofourown.org/users/Cardinal_Rat_Man/gifts).



Sam’s words were still resonating in his ears. 

_It’s not selling._

His eyebrows furrowed deeply, pursing his lips together tightly as he stared down at the liquor in his glass. How was it his problem that the records weren’t selling? That’s why he had a PR team for, right? And the reason for why he signed the contract with Crowley Recordings? 

_Maybe you lost creativity?_

Fucking creativity? Really? Who was Sam to tell Dean he wasn’t creative anymore? Apart from being his manager and his own blood? 

A soft huff left Dean’s lips, letting go of the glass so to bring his hands up to his face. Rubbing over his eyes tiredly, he started convincing himself that he wasn’t the one in the wrong here. If his records weren’t selling as much as everyone wanted to, then it was probably because people’s taste in music was shit. It absolutely had nothing to do with the fact that his writing had become dull and commercial. 

How did his team exactly expect him to be always on a creative peak, when he had been forced to put out a new album each year? Writing was a tough process; and that wasn’t even the half of it all. Composing was excruciating. The fact that Dean was a perfectionist didn’t help. He couldn’t just settle for any song. If he wasn’t feeling it, then it meant it wasn’t even a song. Not really. It was just… noise. 

_They want you to try love songs._

Love songs? There was nothing more commercial than that; Dean was positive about it. He rolled his eyes to himself and ran both of his hands through his hair, leaning back against his couch. The leather creaked softly as he shifted his body weight, it being the only sound that filled the room at the moment. It was too loud for Dean, though. Sam’s words were loud enough already. Any other sound seemed like an explosion in his ears. 

_The last album was too angry, Dean. People aren’t into that._

Fuck people. 

Why the hell should Dean care about what people were into? 

“Good point.” He whispered to himself, as he realized that if it wasn’t for people that started listening to him in the first place he wouldn’t have a career at all. His eyes fluttered close, focused only on the thumping of his heart. At least it was slowing down. Dean had gotten way too worked up during his phone call with Sam. It just had been so unexpected. 

So what if the last album sounded angry? He was indeed very angry. Dean was tired, too. He had put out six albums and gone on six world tours, all in six years. Couldn’t they give him a break? 

_They’re not mad at you, Dean. Just worried you don’t have an actual audience right now. Maybe you need a break?_

Of course he needed a fucking break. Dean had been pushing himself to compose so much he was starting to hate his own instruments. The whole point of dedicating his life to music was to not feel like he was doing a job. But with all the deadlines, marketing issues and NDA’s, it was starting to feel a whole lot like a job. 

Maybe Dean had enough. Maybe he was reaching that dreadful point in his career, where life was telling him that it was time to step down. After all, six years wasn’t _that_ bad. It could’ve been worse. His biggest fear was becoming a one hit wonder. Good thing he was way past that stage. 

He didn’t have much time to continue wallowing in his own misery, since the doorbell to his penthouse disrupted his train of thought. “Come on.” Dean groaned in frustration, sighing heavily. It took a good five minutes and three more of his awfully high pitched doorbell rings to finally get him off the couch. “Can’t I just get five minutes of peace?” He murmured and pinched the bridge of his nose, death glaring at the door before he even reached it. 

“Sammy?” 

“Hey.” Sam smiled small and let out a heavy sigh, raising his eyebrows as he looked over Dean’s appearance. “I see you didn’t take the news very well.” He murmured and rubbed the back of his neck, furrowing his eyebrows in concern. “I probably shouldn’t have said all of it over the phone.”

“Yeah, you think?” Dean scoffed and rolled his eyes, turning around on the back of his heels. He headed back towards the living room, leaving the door open for his brother to come in. “You don’t really sugar coat stuff, you know that?” He muttered, sitting back down where he had previously been. “Thanks for telling me my career is over and that I have no talent over the fucking phone.” 

“What? No. Dean, come on.” Sam shook his head and closed the door behind himself. Sure, Dean could be dramatic sometimes but this was on a whole new level. But then again, Sam should’ve been prepared for it. He shrugged off the jacket of his suit, throwing it over the kitchen counter as he made his way inside Dean’s apartment. “You were told to get some vacations! How is that a bad thing?” 

Dean rolled his eyes and finished his drink, licking over his lips quickly. Of course Sam wouldn’t get it. He pursed his lips together and looked up at his brother, staring into his eyes for a moment. “You really don’t see what’s going on? It’s over, Sam. No one wanted me. And if my last option is telling me I need to get some vacations, I’m pretty sure that means I’m out.” 

The journey hadn’t been easy. Not at all.

When a naive, 17 year old, Dean Winchester decided to drop out of high school to pursue his dream of becoming a successful musician, he was sure he had everything in the bag. It’s not like he believed that a record label would sign him up right away, but he was pretty confident in his music skills. Though apparently talent wasn’t exactly one of the requirements. If it didn’t sell, they weren’t interested. And Dean, well, he wasn’t one to write catchy pop songs that would stream on the radio for weeks.

Dean wanted everything. The sex, the drugs and a whole lot of rock and roll. It just so happened that the music industry didn’t want that anymore. It was too ‘old school’; that’s how everyone described Dean. The green eyed kid thought it was a compliment. He was purposely going for old school. Mötley Crue? AC/DC? Led Zeppelin? How could Dean not want to be old school? How could anyone? 

_Look, kid, you have style. I’ll give you that. But it’s not what we’re looking for in an artist right now._

“Last option?” Sam frowned and loosened up his tie, sitting down on the couch across from his brother. “What are you even talking about right now?”  
“This label. The deal. All of this started because literally no other record label in the world wanted me—” 

“In the _world_? Now that’s just an exaggeration. We didn’t even contact labels outside of the States.” Sam interrupted and crossed a leg over the other. A small beeping sound interrupted their conversation and he dug into his pocket for his phone. Junk email. Why was he still getting notifications for those? He was sure he had adjusted the settings of the app. Sam tapped softly over the moon on the screen, letting out a soft sigh. He didn’t need anyone or anything disturbing him at the moment. He had enough on his plate already with his very distressed brother. “Which was obviously our biggest issue, because as soon as we began searching here in the UK you got a ridiculous amount of offers. So don’t give me that last option crap just because you’re stressing over some bad album sales. This contract deal was far from being your last option, Dean. Your career is not over so please. Just chill out.” 

And he was right. 

Fuck.

Dean hated when Sam was right. Which happened more often than not. He bit the inside of his cheek and looked over at him, letting out what felt like the thousand sigh of the day. “Love songs, Sam. I mean, really? Am I supposed to go all One Direction all of a sudden?” He raised an eyebrow. “I don’t do love songs. I don’t even like them.”

“Bullshit.”

“What?”

“What about those sappy songs from Scorpions and stuff?” Sam hummed, gathering energy for a second before he stood up. He headed for the kitchen, deciding that what Dean needed was a good meal and a beer. That would cheer him up. He wasn’t in the mood to deal with his cranky dramatic ass.

Dean’s eyes almost popped out of his head at such aberration. “Okay, wait, hold up. There’s a difference between a power ballad and a love song, okay? They’re complete opposites.”

“Yeah?” Sam scoffed and looked at Dean over his shoulder for a second, before focusing back on the food inside the fridge. Or really, the lack of it. “How so?” He took out a plate with some odd looking leftovers and scrunched up his nose. There was no need to smell it to know it had expired already. Question was how long ago. 

Dean crossed his arms over his chest and narrowed his eyes at his brother, jaw clenching slightly as he shrugged a shoulder. “They just are. It’s a fact. You wouldn’t understand.” He hummed and frowned as he noticed Sam throwing out all of his food. “Hey! What are you doing?” 

“Preventing a food poisoning death.” 

“Who’s the dramatic one now, huh?” Dean smirked, though it faltered when Sam took out a bowl of green looking pasta. “I don’t remember cooking pesto.”

“It’s because you didn’t. It’s mould, Dean.”

“Oh.”

“When was the last time you actually used your kitchen to cook?” 

Now _that_ was a good question. That Dean honestly couldn’t answer, because he simply had no idea. He bought the penthouse after signing his contract with Crowley Recordings, which was almost six and a half years ago. With the constant touring and the countless hours he spent at the studio, Dean had never seen the apartment as a home. It was just a sort of comfortable place where he could safely sleep at night. But that was pretty much it. Hell, he had been living in London for a while and not even the city felt like home. 

“Never?”

“Exactly.” Sam sighed softly and spun around to properly face Dean. His eyes scanned over his brother’s expression and pursed his lips together in concern. Dean just looked so… tired of everything. “Don’t you think that maybe the record is also worried about your wellbeing? At least, just a little? Because we both know they’re more worried about finances. But they’re still human, kind of.” He laughed softly and crossed his arms over his chest, leaning back against the kitchen counter. “Taking vacations isn’t punishment, Dean. Far from it.”

“Well, it certainly feels like it when they had me working non stop. Now all of a sudden they’re telling me to take a break? What changed?” Dean huffed.

“You.”

Dean stared at Sam in shock for a few seconds, trying to process what he meant with that. Or really, he was just trying to figure out how to avoid such conversation. He could always fake a meeting, say he was late for it. But Sam was the one that was always booking them, so he would know it was a lie. A fake date would work. Dean had a bit of a reputation for sleeping around, so that would’ve been more plausible as an excuse to get the hell out of his apartment. Though going on dates was something completely different from sleeping around. When was the last time Dean went on an actual date? He had no idea, honestly. He didn’t even have a prom to attend to, so he missed out on those shitty high school experiences of a date. 

Had Dean Winchester really never gone out on a date? Huh. Who would’ve guessed. And he was only realizing it himself at the age of thirty. 

It’s not like he couldn’t have dates. But Dean just didn’t have the time for it all. Not because he was afraid that no one would ever like him for who he really is. Not because he decided to escape the possibility of falling in love by meeting people for a couple of hours before ditching them. Not because the idea of being so vulnerable and exposed to someone else freaked him out. He just didn’t have time. 

What an interesting stream of consciousness. Dean was supposed to figure out a way of how to run away from one of Sam’s lectures. Not to dive into his own existential fears of how he perceived loneliness. 

“I definitely need a break.” Dean whispered softly to himself.

“What?” Sam cleared his throat and raised his eyebrows. “I didn’t get that.”

“Nothing.”

“Look, Dean.” Sam sighed softly and ran both of his hands through his hair, tugging at the ends of it gently, before letting his arms fall back to his sides. “All I’m saying is that it seems like you’re not enjoying this life lately. And it reflected on your last album, which is why it didn’t sell and it’s why I’m here today trying to figure out what the hell is going on.” 

It was pretty damn tough to enjoy being a musician when it didn’t meet any of his expectations. Sure, the first two years were amazing. He had the time of his life and the high of being on stage had him levitating everytime he went to bed. But as soon as composing started being not about his own pleasure, but to meet certain standards the label put on him, things changed. 

“I’m just. Tired.” Dean admitted and shrugged a shoulder, sitting down on one of the kitchen stools. “And hungry.” He added after his stomach growled.

“Let’s go out for dinner. You need to eat real food.”

\--

“This is your definition of real food?” 

Dean raised his eyebrows as he stared down at the plate in front of him. The whole meal was the size of his palm. Probably smaller. Why did he trust Sam with his dinner in the first place? Of course he would choose some fancy restaurant where the portions were served for people who clearly didn’t enjoy food at all. 

“Yes, Dean. Because it’s actual food. Not like the usual processed garbage you tend to eat.” Sam rolled his eyes, happily taking a bite of his perfectly seasoned quinoa. 

“Remind me to never let you order for me ever again. In my life.” Dean muttered and furrowed his eyebrows deeply, as he scooped up the entire portion of quinoa from his plate in a spoon. He looked over the brown looking seeds and scrunched up his nose. God, he would kill for a burger. 

The green eyed man placed down the spoon and looked around the restaurant for a moment. The place was awfully loud. He didn’t like it. Which was weird, considering Dean’s life was all about being loud. Concerts, studio sessions, composing, everything. But this was a different type of loud. The noises of everyone talking, cutlery hitting the plates, glasses clinking against each other… Did people actually enjoy restaurants? They were crowded all the time and it wasn’t Dean’s type of crowd either. He bit at the inside of his cheek and rested his elbow on the table, chin on his hand as he indulged himself in his own thoughts. 

“You’re not hungry?” Sam spoke up in concern, interrupting Dean’s silent conversation with himself. 

Dean blinked slowly, his eyes landing on Sam’s, as he raised an eyebrow. “I’m starving, man. But I’m not gonna eat this…” He looked down at his plate once again, before looking back at Sam. The disappointment in his little brother’s eyes was clear. Fuck. Dean cleared his throat and ran a hand through his hair, scratching at the nape of his neck once he reached the soft ends of his short hair. “ _Only_.” He put on his best smile and forced himself to eat the spoonful of quinoa. “We can’t just have only this, right? I was thinking of dessert, y’know. Got distracted. Do you think this place has pie? Or is it too fancy for that?” 

It was a nice save. Sam’s expression returned to normal and they engaged in casual small talk. Dean wasn’t really listening, though. He picked up the most important pieces of information, so to nod occasionally and let out soft ‘oh’s and ‘yeah’s to keep the conversation flowing. But his mind was clearly elsewhere. 

“How long?” Dean cleared his throat, looking up at Sam. The other man was mid sentence talking about how wonderful the married life was. Dean wanted to be happy for him. He was, really. But he couldn’t get the label’s idea of a break out of his head. 

“What?” Sam’s lips parted, staring at Dean in confusion. “How long have I been married?”

“No.” The musician sighed heavily and rubbed his face tiredly with both hands, pursing his lips together for a moment. “This… _vacation_. How long does it have to be? Because it feels like they’re letting me go.” And Dean knew he was selfish for making himself the center of attention once again. Did Sam mention something about trying to adopt a dog with Jess? Or was it that they were trying for a baby? Dean didn’t pick it up. He hoped it wasn’t the latter, though, or else he would look like a dick for changing the topic so suddenly. 

“No one is letting you go, Dean. How many times have I told you this already? I’m your manager, remember? If your contract was ending I would know.” Sam pointed out and took a sip from his wine. 

Dean narrowed his eyes at Sam and examined him for a second. He seemed relaxed. Good. That meant it wasn’t baby talk he was ignoring. 

“How long do you want it to be?” 

What?

“What?” Dean voiced his confusion and shook his head. “I don’t even want it at all!” He did. 

“A year hiatus? Six months? Three? One?” Sam offered, taking out his phone so to check through the calendar.

“I-”

“Let’s start slow.” Sam offered, humming softly as he stared at the screen of his phone. “How about one month? I know you want to be back in the business as soon as possible, but I also need you to get some rest. For real. Get proper sleep once and for all. At Crowley’s they want you… revitalized. Many artists go away to write their albums, you know? It wouldn’t be a bad idea to go on vacations for a month. Get some fresh air and gather new ideas without the pressure of meeting a deadline. Sounds good?” 

“No.”

“Dean, come on.”

It was hard to let go of everything. Working his ass off to achieve his dreams was the only thing Dean knew how to do. He didn’t finish school, which meant going to college wasn’t an option. Music was the only thing he ever had in mind. And now he was supposed to let go of it? For an entire month? 

“You need this and you know it.” 

“Fine.” Dean rolled his eyes, moving his glass slowly, watching the whiskey in it swirling around the ice cubes. “But I’m not writing love songs. So you can tell them to forget about it.” 

And that’s how Dean ended up on a plane.

How exactly did it happen? He had no idea. Well, he did. But he’d rather not think about it at the moment, or else he would end up regretting every decision made over the past three days, which would lead him to leave the plane. Dean was willing to jump off it with a parachute if it was necessary (not really).

After ordering an extra large pizza for himself and having a couple of beers after his dinner with Sam, he decided to call Bela. He wouldn’t have been able to rest unless he heard it from _them_ that they weren’t cutting Dean off. He actually tried Crowley first, but of course the asshole didn’t answer. He never did. So, the other British was his only other option. Dean didn’t really know many people at the label. Sam was usually the one that dealt with the legal stuff, which meant that Dean allowed himself to step back from it all. Having your lawyer brother as your manager definitely had some perks. Except for when Dean had to do things for himself and he didn’t know who to contact. He made a mental note of getting more involved with the people that worked with him. 

_We could never let you go, love_ , she said with that awfully smooth accent of hers. Dean had convinced himself he wasn’t attracted to it. Not only was Bela practically his boss, but she was also a pain in the ass. Dean was sure they had a thing going on at first, but it turned out that she was just using her sex appeal to screw with his young, innocent, mind. Not quite young, really, and definitely not at all innocent, but that was Dean’s version of the story. 

After the two hour long phone conversation, three quarters of the pizza down and two beers in, Dean decided that Sam was right (yet again). No one was looking to get rid of him at the label. They were just concerned about him (concerned about their money, really, but it was enough for Dean). The fact that he was even doubting himself so much indicated that something was wrong. Because he was never like that when it came to music. He realized that if he wasn’t confident enough in his own songs, it was because for the last couple of years he had been composing out of obligation and not pleasure. 

One month wasn’t even that much. No one would expel him from the music industry for taking a small hiatus. Bela even gave him the green light for extending that month for as long as he needed to. Dean always knew that deep down the girl cared about him. Very, very, deep down in her heart.

Dean ran a hand through his hair, inhaling shakily as he tried to gather himself, looking out the window at the runway under them. The ground seemed so distant already and they weren’t even in the air. But once they were, the engines would fail and his mask wouldn’t work and the pilots would get heart attacks and they wouldn’t have the slightest chance of salvation. Dean was sure of it. 

“First time flying?” 

Dean had gotten used to all the British accents and could perfectly distinguish them by country, sometimes even by region. But he couldn’t quite put his finger on what this accent was. It was thick and not very British at all, really. 

His head snapped to the side quickly, looking up at the man that was standing in the aisle, leaning against the seat next to him. What was up with people making casual conversation with strangers? Dean thought that only ever happened in movies. God knew he would never try to engage with people he didn’t know just for the sake of it; much less in a plane. 

“No.” Dean scoffed softly to himself and raised his eyebrows, with a slight shake of his head. “If anything, it’s too much flying.” He murmured and scratched over his jaw line, sighing heavily as his hand fell back down to his lap. 

The worst part of touring was that Dean had to get on way too many airplanes for his liking. But what else was he supposed to do? It would be a waste of money to ship the Impala to every continent and spending days, maybe even _weeks_ , at sea sounded even more awful than being up in the sky for a few hours. With cars and boats out of the question, there was only one option left. It wasn’t ideal, but it worked. 

The man nodded and stared at Dean for a moment, biting at the inside of his cheek. When he noticed that the green eyed man made absolutely no effort to move, he cleared his throat and raised an eyebrow. 

“That’s my seat.” 

Dean’s lips parted and looked up into a pair of piercing blue eyes. Were those contacts? No one had eyes that blue. “What?” He blinked quickly in shock, laughing nervously. He was already anxious for the flight itself. He didn’t need anything extra to add to it. He dug his hand into his pocket and took out his passport, furrowing his eyebrows as he picked up the boarding pass placed between the pages of it. “Nah, man. Pretty sure this is my seat.” Dean murmured as he looked over the seat number on his ticket.

“Huh. Weird.” 

The guy had to be European. Dean had been scratching at his brain for the last few seconds, trying to figure out what was up with that accent. He was sure he had heard it before, considering he had been to almost every country in Europe. But he still couldn’t quite put his finger on it. 

“I guess I’ll just sit here, then.” The man hummed as he accommodated himself on the empty sit besides Dean. He checked his digital boarding pass after putting his seatbelt on, just to make sure he didn’t make a fool of himself. “I guess it happens. How did that one saying go? Airplanes fall, how could a man not?” He hummed in thought, tilting his head to the side slightly. “Can’t remember. My mother used to say it all the time, though. Something about how it was normal to make mistakes? I mean, science has gone this far with airplanes and they still fall sometimes. It’s okay for simple errors to occur and we shouldn’t condemn them.”

What the fuck?

It was too much information. Dean didn’t even know where to start processing everything. Did the man really give him a life lesson out of an error in the seating arrangement? And who started talking about how airplanes fall when they’re in one? Who was this guy? Dean stared at the brunette in shock and nodded slowly, not really knowing how to reply to all of that. They didn’t even know each other and they were already talking about science and the moral aspects of human errors? Dean didn’t even let Sam go all philosopher on him and now a stranger did exactly that out of nowhere. 

“Sorry. I talk too much when I’m nervous. It’s my first time flying.” 

“Yeah. It shows.” Dean murmured and raised his eyebrows. He was in no position to judge, though. If it wasn’t because he was so used to flying (not by will), he would probably be in a worse state than this dude. 

“Castiel.” He smiled warmly and stretched out his hand for Dean. “Cas.” He offered.

Who the fuck was called _Castiel_? 

“Dean.” The american nodded back and shook Cas’ hand gently, giving him a small smile in return. 

The light above them with the small seat belt sign turned off, causing Dean to frown in concern. Why were the pilots being so reckless? Weren’t they supposed to stay seated and secure for the take off? Dean knew all pilots were evil, one way or another. He let out a shaky breath and secured his own seat belt tightly, just in case. Though when he looked out the window, his eyes widened in surprise. 

Clouds? Why was he seeing clouds already? When did they even leave the ground? Dean’s eyes widened in panic, lips parting as he took in a few shaky breaths. Did he pass out in fear and woke up already in the air? He doubted it but, honestly, it was a very possible scenario.

“When did we uh…” Dean cleared his throat and looked up at the man sitting besides. The ice was long broken with Cas’ previous rambling. He hoped his confused state wouldn’t make things weird for the next couple of hours. Dean had traveled with some weird passengers before and it was never pleasant. “Take off?” He murmured and rubbed his neck nervously, biting at the corner of his lower lip gently. 

Cas furrowed his eyebrows back at Dean, staring at him for a moment. Was he serious? It had probably been one of the shakiest take offs ever. Well, not like he had a reliable opinion since it was his first time experiencing it. Dean mentioned he had been flying for a while, though, so if he didn’t feel it then it was probably a pretty smooth one. Although if that had been a smooth one, Cas didn’t want to know what a bad one was like. He bit the inside of his cheek and shrugged a shoulder.

“Like five minutes ago, maybe?” 

“What? And I didn’t pass out?” 

A small chuckle escaped past Cas’ lips, eyeing over Dean curiously. Was the guy high or something? His pupils looked normal, though. “No.” He scoffed, staring into his eyes for a second. They reminded Cas of the apples he grew back home. “Was that supposed to happen? Is it a regular thing? You passing out during take offs?” 

“No.” Dean rolled his eyes and scoffed, running both of his hands through his hair. His fingers laced gently together with each other at the back of his neck, sighing shakily as he tried to relax. “I just always notice take offs.” 

“Oh. I’m sorry I distracted you. We took off while we chatted.” Cas hummed and shrugged a shoulder, as he took out his headphones and a book from his bag. “Or really, I talked a lot and you just stared at me weirdly.” He laughed softly.

Wait. Dean had been _conscious_ during take off? Like, an alive and functioning human being? And he didn’t notice his worst nightmare happening? Or one of the worse, at least. Nothing could ever top the plane crashes. Ever since he stepped on a plane for the first time in his life, he had always been hyper aware of his surroundings. Then all of a sudden take offs were smooth enough for him to ignore them? 

Several people had tried to calm down Dean when flying before. Sam was the one in charge of that task most of the time, but it never really worked. Jess usually did a better job at it whenever she decided to join them for tour every once in a while. It was tough making long distance relationships work, so she made sure to have some free weeks to travel with her favorite boys every semester. But not even her could fully soothe Dean.

So what did this guy have that the people closest to him didn’t? It didn’t make any sense. Maybe Cas’ little monologue had been so disturbingly odd and boring that caused the musician to lose awareness of the plane. Sounded improbable, but not impossible. It was also the only reasonable explanation Dean had to the entire situation. 

Dean refused to call it destiny. Such a thing didn’t even exist. But it was indeed a curious situation considering he was on that flight to get away from everything for a while and find some inner peace. It was definitely a good way to start vacations by not being frightened to death by take off. It was certainly more than what Dean could understand at the moment, but he didn’t have enough energy to continue trying to decipher the situation. He had never been so thankful for a boring life lecture before.  
The last thing he heard before of the guy sitting next to him was him calling over a flight attendant for a glass of water. 

And then he woke up. 

His eyes fluttered open slowly, trying to adjust to the light once again. Dean’s lips parted, eyebrows furrowing as he looked around the half empty plane in confusion. Had they arrived already? He rubbed over his face gently with a single hand, running the other one through his hair. What an odd day. Not only did he not realize when the plane took off, but he also _fell asleep_ during the flight? That never happened. Being restless was the normal sensation that usually engulfed him whenever he had to fly. But then again, he wasn’t going to question it.

The blue eyed man was nowhere to be seen. No passengers from the business class were around, either. They all probably got off the plane long ago. Why did no one wake him up? 

The worst thing about traveling was all the airport duties one had to go through. Getting your bags was exhausting enough. And all the security and stuff? Yeah, Dean was definitely not up for it. Although he was very glad his feet were on the ground once again. That was indeed very reassuring and it lifted his spirits up a bit. 

Sam had told Dean he would fall in love with Italy and he was absolutely right. It’s not like Dean hadn’t been in the country before. He had played several shows in Rome before, but he had never actually gone touring. He usually stayed three days at most in the city, in order to get some rest before the concerts. Sightseeing was not a typical activity in his schedule whenever he was on tour. Maybe if he had spent some more time relaxing during his trips he wouldn’t have ended up hating traveling so much. 

Dean was still at the airport and he was already enchanted by Pisa. He allowed himself some time to go through the souvenir stores and just by staring at the fridge magnets with pictures of the city, he was sure he was in love. He would have to come back to the city sometime in the future, so to properly explore it. There was so much history to relieve walking through those streets. But Sam had told him he needed to find a place to get away. Staying in Pisa would’ve involved a lot of tourism and tourists, which Dean wasn’t really in the mood to deal with. He was tired of people. 

After getting himself a ‘I love Pisa’ scarf and a snowball with the tower of Pisa in it for Sam, he headed out of the airport. He bit at the inside of his cheek as he went through his phone, checking over the small itinerary Sam planned out for him. No one could actually call that an itinerary, though, really. It was a single bullet point that said ‘bus at 15:00. Tuscany’. 

Dean stepped out of the airport and closed his eyes for a moment, allowing himself to just _breathe_. Maybe he was going insane, or being in a plane without panicking fucked him up, but he was positive that even the air in Italy smelled different. Cleaner, maybe? He had no idea how polluted Pisa was in comparison to London. He couldn’t care less, honestly. It smelled like freedom. Dean had been working his ass off nonstop for six years. He could allow himself to be a tad dramatic. 

Once he opened his eyes again, the bus he needed to get on had parked right in front of him. Life was really being a sweetheart to him. He wasn’t sure what he did to deserve it, but he wasn’t going to complain about it. He grabbed his luggage and walked over to it, making sure it was the same Sam indicated, and got in. 

The ride from Pisa to Tuscany was about an hour long and then about half an hour more to the hotel. And honestly? Dean wished it was longer. He couldn’t get enough of the view. Everything was just so damn _green_. He was having trouble believing his eyes. His lips parted as he stared outside the window, enjoying the soft sound of the engine rumbling and murmured conversations in Italian. Dean was already starting to think that one month would definitely not be enough time.

Sam had insisted Dean stayed at a vineyard hotel. Why? Dean had no idea. What was the fun of staying at a winery? He didn’t even like wine. The younger Winchester insisted that he had to try the Chianti wine, that it was one of his favorites and one of the best in the world. Dean really couldn’t care less about wine. He tasted it once when he was sixteen and decided it was the most disgusting drink ever. Why would he ever go for wine considering beer was a thing? Or vodka? Or whiskey? There were so many other alcoholic options that he actually enjoyed. But Sam insisted on how staying there would be a unique experience that Dean couldn’t miss. It was ‘a totally romantic destination’, as he put it. The rockstar saw no interest in spending a whole month in a romantic getaway location, considering he had no one to share said experience with. What was the point? If Sam had sent him to forget about the world at a place where everyone would be taken and lovey dovey all the time, Dean would make sure to destroy him. That was the last thing he needed. 

“Holy-” Dean’s eyes widened as he stepped out of the bus. 

There were no words to describe the place. He was stunned and breathless. Dean didn’t know what to call the building at the top of the hill. It was too small for a castle but too big for a house. It didn’t even look like a hotel. He was honestly clueless as to what it was, but he was in love with it. He felt like he had just stepped back the XVIII century, but with all the benefits of the XXI one. 

Huge trees lined up along the path that lead to the house, each one more majestic than the other. The soft breeze made the branches dance swiftly, causing some flower petals to fall to the ground. The whole scene felt surreal, nature seeming to engulf the strange presence of Dean’s persona that clearly didn’t belong there. He felt as if he was disrupting the environment and a pang of guilt built up in Dean’s throat, as a flower fell from an apricot tree. It hit calmly against his cheek, not being able to continue the course the wind decided for it. The green eyed man blinked a few times, forcing himself to adjust his senses back to reality. He reached up to his face gently and held the flower gently between his thumb and index finger, staring at it in awe for a moment. His eyes fluttered closed, lashes caressing the top of his cheeks gently as he brought the flower to his nose and breathed in it’s scent. It was intoxicating. 

Everything was ridiculous. A thirty year old man wearing all black, combat boots and leather jacket included, being the proper stereotype of a rock musician, was captivated by a flower? Who would’ve guessed? Dean Winchester had a soft spot. He was sure that to anyone else he probably looked crazy; like he had never in his life seen a flower before. Not like he cared. He was having a moment. 

The sound of people walking past him and uphill startled him. Dean’s eyes snapped open, looking around quickly just to make sure no one had noticed him. Many probably had, but he decided to ignore it and believe his own lie. He absolutely didn’t go soft for a God damned flower. It was his first day of vacation and he was already appreciating the small things of life. Sam would be proud of him. Not like he would actually tell him what happened. 

“That look on your face is exactly why I opened this place to the public.”

Dean wasn’t expecting for anyone to talk to him. Hearing someone else’s voice was… odd, to say the least. He had sort of been mentally preparing himself to isolate for an entire month and have no actual human contact at all. That clearly didn’t last very long. 

“What?” Did he look so foreign that this person decided to go for English immediately? Dean had been hoping to try out his awful Italian. Though he doubted Italians would be pleased upon hearing him. 

He turned his head to the side slowly, eyes widening some as he stared into those deep blue orbs from a few hours ago. It was the weird man that had soothed take off for him. It wasn’t really like _that_ , but the effect was the same, so Dean went along with it. What was he doing there? Had he followed him? Maybe he was a crazy fan and wanted an autograph. It wouldn’t be the first time someone got a hold of his movements and followed his locations. 

Cas let out a soft laugh and shook his head, as he stared at the flower Dean was still so delicately caressing. The green eyed man rubbed his thumb slowly over the petals, one by one, and the Italian couldn’t bring himself to look away. It was almost like watching a living oxymoron. The man clearly wasn’t familiar with nature and it painted a hypnotizing picture. Cas usually never recieved people like Dean. Not because he didn’t want to, but because they didn’t come at all in the first place. His winery wasn’t exactly an attractive location for people like Dean. Even though Cas knew he was being completely judgemental about it. Maybe there was more to the musician than met the eye. 

“You know, that first interaction with this place. It’s out of this world, isn’t it?” 

Dean nodded in agreement, his eyes scanning over Cas’ features. “Heavenly.”

That was an interesting adjective for sure. Cas had used it himself but it was the first time someone else used it too. His grandfather must be grinning up in the skies to himself. When he passed and left Cas as the owner of, well, everything, he told him to make people happy with what they had. Dean’s words were reassuring. It was good to know he was on the right path. 

“I’m glad to see you didn’t stay sleeping in the plane.” Cas teased and began to walk ahead, humming softly to himself as he stuffed his hands into his pockets. It was only then that Dean realized that the man wasn’t carrying any luggage with him, except for the small traveling bag he spotted earlier in the flight. 

“Yeah.” Dean rolled his eyes at that and picked up his luggage, quickly catching up with the Italian after a few quick strides. “Thanks for leaving me there.” He raised an eyebrow, smirking slightly. “You travel light?” He nodded at Cas’ hands and the clear lack of belongings with him. 

“There’s no need for bags if I’m coming home.” 

Which, strange, but okay. Dean wasn’t going to question this guy. He didn’t even know him. Maybe it was Italian culture? He had no idea and he wasn’t going to risk it. It was better to stay quiet rather than risk coming off as rude. Still, the fact that he traveled from London to Italy with no bags at all didn’t sit right with him. Who went to another country without anything with him? But then again, what more was he supposed to expect from a guy that went on with a sort of philosophical discourse with him after knowing him for less than five minutes? 

“Home? You live at the castle?”

The accent Dean couldn’t quite catch before made sense then. Of course the blue eyed man was Italian. Maybe if he had actually used his brain a bit, he would’ve been able to figure it out earlier. Traveling from London to Italy with practically no bags? Plus a thick accent? Dean should’ve seen it coming. Although, he had no idea of how to know Cas didn’t bring any luggage with him.

“Castle?” Cas raised an eyebrow and scoffed softly, looking at Dean over his shoulder for a moment. He held eye contact between them for a split second, an odd rush of sensation rushing up his spine at it. He couldn’t quite put his finger on what it was. He just knew that he didn’t mind it. “There are castles in Italy for sure. This is not one of them, though. It’s just a humble winery.” He hummed, tilting his head to the side slightly. 

Humble? Dean was positive there was nothing humble about the incredible architecture that displayed before him. He could already spot two pools and three houses. He assumed one of those had to be the actual winery. Another one for sure had to be the hotel. And the third one? Well, Cas said he lived there. So one of the buildings was probably his home. It all looked gigantic and like it was worth a billion dollars. Dean had no idea how much he paid for his one month stay at the hotel. He told Sam he didn’t want to know. He just handed his little brother his credit card and told him to arrange everything for him. 

“And you decided to live in a winery?” 

Why was Dean asking so many questions? He had never been the kind to actually start conversations to get to know other people. He bit at the inside of his cheek and swallowed nervously once he realized he was probably overstepping. 

“Sorry.” Dean laughed softly and cleared his throat, with a shake of his head. “You don’t have to answer that. I promise I’m not usually this nosy.” He offered Cas a small smile and a shrug of a shoulder. 

“It’s fine.” Cas reassured. “I inherited it.” 

Well, damn. Dean wasn’t exactly expecting that. Was the guy rich? He had to be. And why was he so surprised? He was rich himself. Though in Dean’s eyes there was a clear difference. Before, he barely had enough to buy food and pay rent. Money started coming along the way because of his hard work. Cas, on the other hand, just got it all on a silver platter. 

The American mentally slapped himself on the back of his head. What the hell was that thinking? He just sounded petty and resented. Dean furrowed his eyebrows deeply, focusing his eyes on the ground instead as he walked along with Cas. He was too embarrassed with his own subconscious mind to look at the other man. He was sure that if he did so, the other would know exactly what he had been thinking about. 

Cas noticed the lack of response and he already knew what Dean was thinking about. It was what everything always thought whenever he told them how he got everything. He smiled sadly to himself and let out a soft sigh, considering whether or not he should address the topic. Probably not. There was no need to go into detail about his life with a random guy he met a couple of hours ago, anyway. 

“I hope you enjoy your stay here.” Cas spoke up after a few minutes of silence, once they were near the hotel’s reception. “I’m usually always around to make sure everything is okay. So if you ever have any complaints, just search for me. I’m not hard to find.” He hummed and stared at the hotel’s main doors for a second. He turned to face Dean once again and eyed him up and down subtly. “ _Ciao_!” Cas spun around on the back of his heels and began to head back home. 

Dean stared at the man walking away, heading towards the house a few miles away from the hotel, situated on a slightly higher hill. The sight of the vineyards was probably amazing from there. He couldn’t quite make it out because of the distance, but he was pretty sure there was a staircase that connected the house down to the vineyards. He wondered if that had been a modern addition to the place, or if it came with the Italian’s ancient looking home. 

“ _Ciao_.” Dean spoke softly, once Cas was out of hearing distance. He probably said the word wrong and didn’t want to make a fool of himself with the strange, attractive, Italian man he just met. There would be plenty of time for that, considering he would be spending a month practically in the guy’s home. 

The woman that checked him in was sweet. Way too sweet. Like, genuinely sweet. It was strange. Were all Italians like that? Dean doubted it. He wasn’t used to it. He had stayed at several hotels, all around the world, and he was certain he had never encountered himself with such hospitality before. Maybe his team just sucked at choosing where to stay whenever they were on the road. 

“Oh, Sammy, I love you.” Dean whispered to himself as soon as he stepped into his room. His eyes widened slightly, lips parting as he took in what would practically be his home for the next month. 

Luxurious was the only way Dean could use to describe his surroundings. There was nothing modern about it and he was glad for it. Otherwise it would’ve been too off putting considering the rest of the place. But it wasn’t. It was perfect. His fingers grazed over the wardrobe, admiring the fine woodwork done with it. Jade orbs ran quickly all over the room, trying to take in as much detail as possible. It was fair to say Dean was overwhelmed.

He kicked the door close gently, placing his bag down by the body mirror. That was a nice touch. Dean stood in front of it and stared at his reflection for a moment, chuckling softly to himself. There was no way he could continue using his typical clothes in such a place. What the hell was he supposed to wear so as to not look like the edgy teenager that didn’t want to come to the family trip? All his clothes were sort of the same. 

“I need to go shopping tomorrow.” Dean whispered to himself and shrugged off his leather jacket, tossing it carelessly onto the bed. That sounded like a good plan. Except for the part where he had to leave the place and actually go shopping. He was in no mood for that. But spending an entire month in tight jeans and band shirts in such an ethereal place would be illegal. 

Dean didn’t leave his room for the rest of the day. He took a shower, ordered room service for dinner and lounged on the couch of the small terrace of his room for the rest of the day.

The familiar itch in his hands overcame him soon enough and he tried his best to ignore him. He had promised Sam he wouldn’t do any writing for four weeks and it was already harder than what he expected. He bit at the inside of his lower lip and closed his eyes, inhaling a few shaky breaths as he tried to envision the proper lyrics that came into his mind. 

They were trash. Just like his last album. Of course he knew his latest production had been a failure. That didn’t mean he wouldn’t defend it in front of others, though. There was no point in composing anything at the moment if he was creatively drained. He would just end up hating his own works in the morning, just like it happened a year ago. Dean told the label he wasn’t up for putting out another record, yet they insisted and it resulted in an awful piece. He couldn’t believe they had the nerve to call him out for the bad sales. Just thinking of the entire situation was enough to dampen his mood. Who thought that forcing an artist to make content was a good idea? 

Instead of searching for his pen, Dean reached for his cigarettes. He was quitting. At least that’s what he had been saying for the past decade. He placed one of the familiar nicotine sticks between his lips, eyebrows furrowing slightly as he lit it up. After taking in a few long drags of smoke, he felt better. He needed to stop worrying about Crowley and Bela and the sales. It wouldn’t do him any good. 

Dean continued smoking his thoughts away, watching the blue sky turn into a velvety orange as the sun began to disappear for the day, until all colour was drained from above. His eyes widened in surprise as he stared at the several stars that began to decorate the sky. It was beautiful. The last time he saw so many stars with such a clear sky was when he went camping with Benny back in high school. Now those were some memories he didn’t mind recalling. There weren’t many things that Dean regretted in life, but losing contact with Benny was one of them for sure. 

“I just hope you’re okay, man. Wherever you are.” Dean whispered to himself as he looked at the sky.

With a slow stretch of his arms above his head, the rockstar made his way back into his room. The night breeze was getting too cold for him to be half naked out there.  
Dean got in bed after brushing his teeth and sent out a quick text to Sam, letting him know that he was still alive. He was supposed to text him as soon as he landed but his phone died during the flight. He would’ve noticed, he _should’ve_ noticed, but he was sleeping. He made sure to explain why he hadn’t texted sooner and turned his phone off for the night, after plugging it in. There was no need to leave it on, since there were no more alarms. No more schedules. No more anything for an entire month.  


\--

Waking up in Tuscany was… Dean didn’t even know what it was. He had no words to describe it. He just knew he was in love with it. Which was saying a lot, considering he usually hated waking up to the sun on his face. But it felt different. 

He stretched his arms above his head tiredly, eyes slowly fluttering open. The sweet burn in his muscles at the motion was enough to wake him up properly. Dean licked over his lips slowly and crossed his arms behind his head, staring at the ceiling in silence for a few minutes. Even the painting on the walls was stunning; it was cream coloured and had very subtle hints of golden patterns. 

“I can’t believe this is my life.” Dean whispered, eyes slipping shut, allowing himself to enjoy the soft rays of sunshine that slipped through the windows. If anyone had told him ten years ago he would be relaxing on his own in Tuscany, he would’ve laughed. Vacations had never been a thing for him. Dean couldn’t waste away money on going to places for mere leisure when he had Sam and himself to feed. Those times were long gone, though. There was no need to keep dwelling on such matters. 

Dean got out of bed and headed for the bathroom. A quick shower to start the day. But then he saw the tub and decided to indulge himself a little bit. After all, that was his only order right? To enjoy himself? 

Dean had never really cared for baths before. He was a shower guy. It was efficient and he didn’t have to wait what seemed an infinite amount of time to get an exact amount of water to actually be able to clean himself. It was also why he didn’t have a tub at home either. Instead he had a big, glass door, shower with smart technology. He didn’t even have to press any buttons to get it on, since he could just talk to it. People usually thought he was crazy whenever he told them he talked to his shower. 

Though that was until he found himself standing in the middle of a Tuscan bathroom, which had a ridiculously large tub in the middle of it. It was made out of wood? How did that even work? Would the water slip through the cracks? Dean had so many questions and he was probably stupid for asking them to himself. A voice in the back of his head told him it wasn’t actually all made of wood, which was confirmed as he stepped into it. 

It had taken five full minutes for the tub to fill up completely. He timed it. It was far less than what Dean had been expecting, but definitely way more time than what he would be willing to waste during his daily morning routine. Did he even have a routine? Not really. Dean didn’t know another word for it, though, so he stuck with it. 

It was _peaceful_. There were absolutely no thoughts invading his mind. The only feeling Dean cared about at the moment was the lukewarm water engulfing his body. He was so glad he had decided to add the bath oil that was by the sink. The small bottle had a tag that said ‘POUR ME IN THE TUB’. Normally, Dean wouldn’t take orders from inanimate objects. But what the hell, right? 

Everything was too good to be true. And his thoughts were proven correctly when someone knocked at the door. 

“Fucking really?” Dean sighed heavily and rubbed his face tiredly, as he shook his head in disbelief. 

“Housekeeping!” A deep voice called from the other side of the door. Why weren’t they speaking in Italian? It didn’t make any sense. Although, considering all the international tourists, English was probably the safest way to go. Maybe it did make sense. 

It took Dean exactly thirty seconds to gather enough willpower to stand up from his spot. He stepped out of the tub and quickly wrapped a towel around his waist, not bothering to actually dry any of the droplets of scented water that lingered on his body. He was planning on getting back in as soon as he dealt with whoever was at the door, anyway. And if the other person was bothered by his lack of clothing, then maybe they should’ve thought twice before coming to his room at… What time was it? Dean had no idea, but he was sure it was early. 

The musician bit at his lower lip for a second as he reached the door, gently placing his hand on the doorknob. The other person hadn’t insisted on knocking again. Maybe they gave up and left? Dean could just turn around and go back to the tub. But he had already gotten out of it. If he was going to ignore the call, then he should’ve just stayed in the water. 

“This better be important.” Dean whispered softly to himself as he opened the door. 

His eyes widened slightly, a rush of surprise going through his expression, before all his face could show was confusion. “Hey.” Dean murmured, eyeing Cas up and down. “You’re from housekeeping?” He raised an eyebrow.

“No.” Cas laughed softly and rubbed the back of his neck nervously, biting at the inside of his cheek. He hadn’t been expecting for Dean to show up wet and half naked to the door. But then again, that was better than the scenario he had pictured in his head. He thought the American would be sleeping and he hated waking people up. Especially because he knew everyone who came to his villa was to find a place to relax. Making sure his guests weren’t disturbed in their sleeps was the least Cas could do. 

“Then?”

“I thought it would be the easiest way to get you to open up.” Cas explained as if it was obvious, his face emotionless. What was going on? 

“Okay…” Dean cleared his throat and crossed his arms over his chest, leaning against the doorframe, making sure to never break eye contact with the man standing right in front of him. “Well, you have me here. So, what’s up?” He hummed. “If nothing’s going on, I would like to resume my bath.” He laughed softly, nodding down at his body, as if his current state wasn’t already obvious. 

“Ah, yes. I notice the lack of clothing.” Cas hummed and flashed Dean a warm smile, which soon faded away. 

Dean pursed his lips together, eyeing all over Cas’ expression, trying his best to figure out what exactly was going through his mind. Though judging by the look on his face, it couldn’t be anything good. “Did I cause trouble already, somehow?” He groaned softly. It was his first day and he already managed to piss off the owner of the place? Great. 

Cas shook his head quickly at that and held his hands up slightly, going to squeeze Dean’s shoulders trying to be reassuring. Though he soon stopped himself, when he realized how the entire action looked. He bit at the inside of his cheeks harshly, ignoring the burning sensation in his cheeks. He cleared his throat and let his arms fall back to his sides in a rather ungraceful manner, rubbing his hands against the sides of his pants nervously. “I was not trying to-” He looked away briefly, before locking his eyes on wide green ones once again. 

“Hey.” Dean laughed softly, unable to help but feel amused. Of course he understood what Cas had been aiming at. He doubted the guy was perverted and was trying to feel him up just for the sake of it. He had encountered several people like that before in his life and Dean was absolutely positive that this strange Italian man wasn’t one of them. “It’s okay. Don’t worry.” He hummed. It was his turn to be reassuring. He placed a hand on Cas’ shoulder, copying the motion the man had previously tried, and squeezed it gently. “Are you gonna tell me what’s wrong? Am I being kicked out of the country? Someone with my same face committed a series of awful crimes and now I’m being chased instead of my clone?” 

What the hell was this guy talking about? Cas stared at Dean in shock for a moment, letting out a soft chuckle as he raised an eyebrow. “What?” He smiled widely. This guy was insane. Cas definitely hoped that there wasn’t any truth behind his words. 

“Oh, I gave myself away.” Dean teased, glad that any tension going on between them was already gone. If he had to make a fool out of himself for that to happen, then so be it. 

Cas rolled his eyes and slid his hands into his back pockets, ignoring how Dean’s hand was still lingering on his shoulder. He had practiced everything he wanted to say to the man, but of course he forgot everything the moment Dean showed up at the door with his ridiculously toned and wet body. 

“You can’t be here.” The Italian blurted out unceremoniously. 

“What?” Dean’s hand fell instantly from Cas’ shoulder, eyes widening. He lifted himself off from the door frame, not casual and relaxed anymore. “Excuse me, what? Why? Like, in my room? I can’t be in my room?” He murmured and furrowed his eyebrows deeply.

“It’s not your room, we-” Cas started to explain, but was cut off by the other. 

“Not my room? What do you mean it’s not my room?” Dean shook his head and ran both of his hands through his hair, the feeling of his nails raking through his scalp soothing his panic a bit. “But I paid for it.”

Well, Sam had paid for it. But he used his money. Therefore, it was Dean who actually paid for it. Why the hell did that even matter? He had no idea why he was internally fighting himself over who paid for his stay. It was paid for and that was all that really mattered. Unless… Sam didn’t actually pay for it. But if that was the case, then why did the woman at the reception welcome him, check him in and hand him the key to his room? Why was Dean panicking at all? There was nothing to gain out of his current state and rationally, Dean knew that. Though it felt that if he fucked up this one chance of taking a break, then the label wouldn’t let him have any other free time again. Maybe he should change labels. If he felt like a slave then it absolutely wasn’t the right place to make his music. 

_Breath, Dean_. 

The man took in a deep breath, eyes fluttering shut, lacing his fingers together behind his head. Dean opened his eyes once again after a moment, deciding it would be better to hear what Cas had to say first. 

“Sorry.” Dean flashed Cas a weird small smile and nodded. “That was embarrassing.” He laughed softly and bit at the corner of his lower lip. “What were you saying?”

Those words brought the blue eyed man back to his senses. He actually had no idea what had just happened. Cas wasn’t paying attention to Dean’s small break down. The moment the other man flexed his arms Cas zoned out. Part of him felt awful for feeling glad about the man’s agitated state, but it was the reason Dean didn’t catch him staring. 

Cas didn’t really have time for anything, or anyone, other than his business. The vineyard was his grandfather’s legacy and keeping it alive had always been his main priority. Which meant that he always turned down any man that seemed the slightest interested in him, under the excuse of not having time for relationships. But hey, taking care of a fairly popular touristic attraction and making sure his wine deals were going smoothly really meant a lot of effort. Also because he didn’t have a huge finance or legal team working with him. So, Cas had to educate himself in all sorts of new fields to keep his business up and running. Could someone really blame Cas for getting a bit… distracted? 

“Yes.” Cas cleared his throat and forced himself to focus his eyes on Dean’s face, instead of his biceps. “There was a system error.”

Dean furrowed his eyebrows and pursed his lips together, letting his arms drop (much to Cas’ dismay). He placed his hands on his hips and took in a shaky breath, his abs clenching as he did so (which Cas definitely stared at for a moment). “System error?”

“Yes.” Cas sighed softly and pursed his lips together as well, mimicking Dean’s expression. “There was an error with the reservations. We have other guests that booked this room before you. I really don’t know how it happened but when you booked this room, it was actually taken. It shouldn’t have been available on the website. I am so sorry. Considering the severity of this issue, I figured it would be better if I came to personally tell you about it. Also, I want to let you know how deeply embarrassed I am about this confusion. But since they booked the room first, I can’t tell them to not come here.”

“But I arrived here first.” Dean murmured. It’s not that he didn’t understand the situation. Also, he sort of knew that it was him that needed to go. But still, he didn’t want to. He liked it there. He liked the cozy Italian villa, with it’s sweet scented room and it’s stupidly large bath tub. But if he had to go, then there was nothing to do about it.

Dean stared into Cas’ eyes for a moment and let out a soft sigh. There was a genuine apology hiding behind those deep blue eyes. He had been planning on writing a complaint and everything. But after seeing the regret in Cas’ face, he just couldn’t. It was not something that he could explain. Dean just embraced this feeling inside him that told him not to add any more burden to this man. 

“Alright.” The green eyed man sighed softly and smiled sadly, nodding slowly, still trying to convince himself that he would have to leave. “It had all been too good to be true, anyway, you know?” Sam had booked the room with so little anticipation time it even surprised him. The whole misunderstanding made sense, after all. 

“I don’t want you to leave!” Cas rushed out and his eyes widened at his own words. That was definitely not the way he had been planning on saying what was in his mind. “I mean.” He stood up straight and placed his hands behind his back. He wrapped his left wrist with his right hand, digging his nails into the skin there, trying to sooth himself. “I know this was our error and I will never be able to make up for it, considering we don’t have other rooms available in the hotel at the moment.” He sighed. “ _But_ …”

Dean narrowed his eyes at that. But what? He didn’t see how he could stay if there were no rooms left. It was a mistake and Dean wasn’t in the mood to add any more complications to his life at the moment. If he had to leave, then he would just try to find another hotel. It wasn’t like the entire situation was the end of the world. He could’ve been packing his things instead of hearing Cas’ apologies over and over again. 

“I have a big guest room at my place. It won’t cost you a thing. We’ll actually return you your money, considering it was our fault you’re going through all this trouble.” Cas offered and raised his eyebrows.

Was the guy serious? 

“You want me to… stay at your home? For a month?” Dean blinked in disbelief, lips parting slightly as he stared at Cas. Incredulity was written all over his face. “For _free_?”

“Well. My house is in the same residency as the hotel and the vineyard. So, technically you’d still be staying in the same place you decided to spend your vacations at. Just… not in the hotel but in that ugly ass house near by you saw when you arrived.” 

“You don’t even know me. I’m a stranger and you’re just inviting me to your house?” 

“That’s not true, we met in the plane.” 

Why was Cas insisting? If Dean didn’t want to take his offer then he should’ve accepted that and moved on. He would have less to worry about if Dean actually decided to just leave instead. So, why was he actually trying to get the foreigner to stay? _Damn, you’re desperate…_

“Alright.” Dean nodded.

“Really?”

“Yeah.” He hummed and took a step back into his room. “I’ll take a shower and pack my things. I’ll meet you later at the reception and you can guide me to your place.” It was free, after all. It was hard to turn down an offer like that. 

“ _Splendido_.” Cas grinned widely and clapped his hands once. He spun around and practically waltzed down the hall. 

It was the first time Cas had anyone stay with him. He didn’t really have friends. Occasionally, he would bond with some of the guests he constantly received. Though all those ‘friendships’ were always fleeting. It certainly wasn’t what one would normally consider as having healthy and stable friends. And his employees… Well… They all got along quite well, for sure. But it wasn’t like any of them actually wanted to spend any more time than necessary with their boss. In conclusion, Cas was really that lonely that he invited the attractive American, he had known for a day, to stay with him. Cas was positive that to anyone else the entire situation sounded insane. With the apologies and the refund it was more than enough to make up for the corporative mistake regarding the room booking. But there was something else to Dean; something that Cas couldn’t even quite comprehend himself.

Dean watched Cas disappear, as he turned around the corner by the end of the hall, and shook his head. “That’s some awkward dude, man.” 

He closed the door to his room - which was not really his room, after all- and headed back to the bathroom. Dean undid the towel around his waist and let it drop to the ground, sighing heavily to himself as he stared at the tub, still filled with water. It was probably cold. He leaned down slightly and brushed his fingertips over the surface of the water and pursed his lips together. “Cold.” He murmured and reached down to pull out the drain stopper. 

After a quick shower, like the ones he was used to taking back home, he got dressed. Dean pulled on his favorite Led Zeppelin shirt and one of his several black jeans. He made sure to add a bit of cologne as well. Not because he was trying to impress anyone, though. He just liked smelling nice. Sam always said it was his subconscious trying to impress someone, at least. 

Dean was glad he didn’t unpack as soon as he arrived. Part of him knew that it was because he didn’t actually have a sense of belonging anywhere, so he didn’t feel like making himself at home anywhere either. Keeping his clothes in the bag was always way more efficient than in a wardrobe, anyway. But another part of him was telling him that it was destiny. Once again, Dean had to remind himself that such a thing didn’t exist. But there had been way too many coincidences in one day for him to believe that without having at least some doubts. What was up with life pulling him towards the blue eyed man? 

Nothing. It had to be nothing. Dean was probably overthinking, which was not something he was known for doing. So, why start now? He furrowed his eyebrows to himself, trying to pull himself away from his own train of thought and shook his head. It was whatever. There was no actual explanation for what was happening in his life at the moment and there was no need for one. It would only drive him insane if he started questioning every little thing he did. 

After making sure he wasn’t forgetting anything in the room, Dean grabbed his bag with one hand and his pack of cigarettes with the other. If there was one thing he would absolutely miss about the room, was the small balcony and it’s perfect view. He kicked the door close once he was in the hallway, heading towards the elevator. 

It wasn’t long before he found himself standing in front of Cas once again. 

“Follow me.” The Italian instructed as he took the room key card from Dean’s hand, so to gently place it on top of the reception counter. “It’s not going to be a similar room to the one you were familiar with already.”

“Well, I don’t know if familiar is the word I would use…” Dean murmured and his eyes fluttered shut for a second as they stepped outside. The same soft, cold, breeze that had welcomed him yesterday was hitting his face once again. He could get used to that sensation. It was lovely. 

The conversation died there and oddly enough, the silence that followed was comfortable. Dean had never been good with silences. Usually if he wasn’t talking he was communicating through music. He stared at the back of Cas’ neck as they walked and shook his head to himself, suppressing the smile that was threatening the corners of his lips. Life really was surprising him lately. 

“Holy shit.” 

It was Dean’s only reaction to the house. 

Sure, it already looked beautiful and gigantic from the outside. The inside, though? It was something Dean hadn’t been expecting. Mainly because it was modern. But it was modern in a way that it didn’t disrupt the building itself, nor the rest of the place in general. It was fucking beautiful. He wasn’t one that went crazy over decorations and furniture. Far from it. So the fact that he was reacting like that was because the house was really breathtaking.

“Are you an architect or something?” Dean asked as his eyes slowly roamed all over the place, taking in every single detail of the living room he was greeted to as soon as he stepped into the house. 

“No.” Cas laughed softly at that and shook his head. “But I’ll take the compliment.” He hummed and stood on the tip of his toes gently for a moment, unable to help the pride that overcame him all of a sudden. 

The colours were light. There was not a hint of darkness and Dean felt a little bit out of place because of it. He looked down at his clothes for a brief second and bit at the inside of his cheek. His black attire was highly contrasting with the light caramel walls. If he had been worried about looking like the edgy teenager that didn’t want to go on vacation before, now he certainly played the part. 

“Are you just going to stand there all day?” Cas asked softly, looking over his shoulder at the dumbstruck man in the middle of his living room. 

“Wha-” Dean blinked quickly and spun around quickly, turning to face towards the direction the voice came from. He bit at the inside of his cheek, noticing Cas was already in the middle of the staircase. He huffed softly and quickly caught up with the other man. 

The Italian led him to his new room and sure, it was not like the bed he had stayed the previous night. Dean couldn’t believe it was better. 

“Are you sure about me staying here? Because I don’t know if I’ll be able to leave after the month is over, first warning.” Dean whispered under his breath, eyes wide as he looked around the room.

It was so fucking big. For a second, Dean worried Cas had taken him to the main room instead of the guest one. He also realized he didn’t have to worry about missing the small balcony from the hotel room, because the balcony he had now was probably the size of the hotel room itself. He placed his bag down on the bed and quickly made his way out towards it, so to take in the view. 

“This is amazing. I can’t believe you live here. I thought the hotel was incredible but this is… It’s out of this world, man.” 

And it was. It was out of this world. Cas thought so too. Although he was pretty sure they were thinking of different things. Why was he so attracted to this man? He had never been worried about his feelings but he couldn’t seem to stop them. He bit at the inside of his cheek and tilted his head to the side, staring at Dean’s face. He had only known him for a fucking day. But still, Cas knew that Dean was the most beautiful man he had ever laid eyes on. 

“Granny Smiths.” Cas spoke up as he stepped out into the balcony as well, staring into Dean’s eyes. The sun was hitting the American’s face in just the right way that made his eyes look a bright shade of green. He leaned against the railings of the balcony and closed his eyes for a moment. It was the only way he could currently think of how to stop staring at the man. 

“What?” Dean hummed softly. 

“Your eyes.” The Italian explained and nodded some, laughing softly to himself. He really wasn’t being the most coherent person at the moment. “They remind me of the colour of the Granny Smiths my mother used to grow. I still have some apple trees here and there.” Cas hummed and looked over the several rows of trees in his lands. 

Dean stared at Cas in slight shock, feeling dumb. Was he supposed to know what the other man was talking about? “Grandma who?” He asked nervously, not wanting to look ignorant. Although that was exactly what he was and there was little he could do to hide it. 

“Green apples?” 

“Oh.” Dean nodded and scoffed. “Yes, of course. I know green apples. Was never a fan of them, though.” 

“Yeah, I get the feeling you’re not really a fan of natural food.” Cas teased and sighed softly as he pushed himself off the railings. He stretched his arms above his head for a second and turned to Dean once again. “Well, make yourself at home. Once again, I am so very sorry for what happened with your room. I really hope this can make up for it. Enjoy your stay.” He smiled warmly and gave him a single nod, before heading out of the room. 

\--

The first week, Dean met Charlie. 

He noticed a redhead sitting by herself during lunch and decided to offer her some company. Dean didn’t know her, but then again he didn’t know anyone. And if he was already going to spend a month in the place, he might as well try to get to know someone. Everyone else was either with their families or their clear significant others, so his safest choice was to go with the lonely woman sipping lemonade. 

“Hey.” He pulled off his most charming smile, tilting his head to the side slightly as he stood in front of the stranger. “Is this seat taken?” He nodded at the empty chair right across the woman on the small, round, table. There was nothing that indicated him that someone was already sitting there. The lack of cutlery, plates and glasses made it pretty obvious. But Dean had no idea how else to start a conversation. 

“No.” The woman answered, without even glancing at the man. 

“Oh.” Dean’s face lit up slightly and nodded slowly. “Well, then I-” 

“I said no.” Charlie frowned deeply as she looked up at the stranger. Did he think it was normal to randomly go to sit with people he didn’t know? “Not interested.” It was probably just some other jerk trying to flirt with her anyway.

Dean blinked, startled, lips parting as he stared at the woman in slight shock. “Not interested in…?” His game really had to be off for him not to realize the redhead thought he was trying to flirt. The green eyed man didn’t even have a game. Flirting had never been a necessity for the past ten years or so. Sure, when he was a teen it seemed everything. But as he grew up, he realized that people were just naturally drawn towards him. Which was also really great for him because he was actually way too afraid of rejection to actively seek someone. Everything was easier if he was the one turning them down instead. 

“You.” Charlie let out an exasperated sigh, placing down the glass she had been holding. She licked over her lips quickly and raised her eyebrows at Dean, waiting for him to realize that was probably his cue to leave. 

“Me?”

“Lesbian.” Charlie pointed at herself with her thumb, quickly shifting his hand position so to point at Dean with her index finger instead. “Man. Not interested. Move along.” She sighed tiredly and picked up her bag. She placed it on her lap and dug through it quickly, until she found the earphones that would save her from the current situation. There was nothing music couldn’t save. 

Dean raised an eyebrow at that and couldn’t help the cackle that resonated through his chest and past his lips. “ _What_? I’m not here to flirt with you.” He raised his eyebrows in disbelief. 

“You’re not?” Charlie asked in slight shock. Dean could’ve sworn she almost looked disappointed. 

“No.” Dean shook his head and pulled out the chair and sat down on it. He placed down his plate of food and stared at Charlie for a few seconds. Once he noticed the girl was making no efforts in ignoring Dean anymore, by putting her earphones back in her bag, he spoke up again. “I dig your confidence, though.” 

The rest was history. For the remaining days of the week, every single activity that Dean planned involved Charlie. 

The two of them decided to visit the actual winery, agreeing that if they were already staying at the place, the least they could do was learn a little bit of how it’s wine was made. Charlie was the most excited out of the pair. She was a sucker for wine, Dean learned. On the other hand, he was bored out of his mind. Maybe if the place made beer things would’ve been different. But there was nothing about the whole process of how to make wine that particularly caught his attention. Not even the wine itself seemed any special to him. Sure, it was super sweet - which was weird, considering every wine he tasted before was shit- and there was _something_ to it. He didn’t know _what_ exactly, but it was something he had never ever tasted before. It was new, but unamusing. 

“It’s the Chianti magic.” Charlie scoffed, hitting the back of Dean’s head at his careless attitude. She didn’t understand why Dean decided to spend his vacations at a winery hotel if he didn’t even like wine. Even after the musician explained everything - who he was, what happened with his sales, his brother telling him to take a break- it still didn’t make sense. Shouldn’t have Sam sent Dean somewhere he actually enjoyed? But then again, Dean didn’t look like he was having a bad time. It seemed pretty impossible, anyway. The entire place was paradise on Earth. 

During the course of that week, Dean also learned Charlie worked for Apple. 

“I thought you hated big companies.” Dean hummed, walking side by side with Charlie through the never ending grape vines. The scent of the fresh fruit was intoxicating. His entire body seemed wrapped up by it and he wasn’t even standing that close to them. Dean would never get used to the whole nature thing. It was a new world to him, but he liked it. Though it was definitely something for him just to appreciate every now and then. The city was where his heart truly was at. Mainly because cities had stages. 

“I do, but- _No_!” Charlie gasped loudly, eyes widening as she noticed her friend reaching out with his fingers for the unripe fruit. Her own quickly wrapped around Dean’s wrist and pulled his hand away from the purple orbs. “What are you doing?!” 

“Touching it?” Dean raised an eyebrow and blinked quickly, confusion written all over his face. “What’s up with you? It’s not a big deal.” 

“Not a big deal?!”

And after a few smacks at the back of his head, Dean was reminded of what the girl that guided them through the tour of the place said. Well, he didn’t really quite remember exactly what she said. But small fragments of her words came back to his mind and judging by Charlie’s reaction, it was clear that touching the fruit in such an early stage wasn’t allowed. It fucked up the process or whatever. 

Charlie eventually explained that even if she did hate big companies, the job she was offered was too good to say no to. She didn’t tell Dean that her mother had cancer and she would do anything to help with her treatment, even if that meant selling her souls to the business people she despised the most. It would be worth it if it meant she could pay for her mother’s chemotherapy. She was sure that her eyes gave her away, though, because as soon as she explained to Dean the money was to help someone she loved, it was obvious he assumed the worst. Luckily for her, the man was decent enough to not ask any questions. Her mother eventually told Charlie she needed some time to take care of herself too, and that’s how she ended up in Tuscany. 

Overall, the two developed a pretty quick friendship. She had been responsible for Dean deciding not to go shopping for new clothes after all. Something along the lines of Dean worrying more about what the rest of the people thought about him, instead of him just being his true self, was more than enough for Dean to regret even considering changing his style. 

Said friendship, obviously, involved a lot of teasing. Which most of it was one sided, really, but it wasn’t Charlie’s fault Dean gave her so many reasons to do so. 

“Don’t you think that’s a little… intense?” The redhead asked one night, after interrogating Dean about why he never headed towards the hotel whenever they called it a night.

The man shrugged a shoulder as they stared up at the bright stars in the clear night sky. Dean almost felt bad for the smoke he was exhaling, because it meant that he was adding to the pollution that prevented everyone from experiencing such a view. 

“I mean, everyone here knows Cas. I’ve never met anyone so invested in their business that actually takes the time to meet every client that arrives at their hotel. It’s nice.” Charlie continued and picked up the bottle of wine she ordered, so to gently pour herself a glass. She raised an eyebrow at Dean and nodded towards the empty glass besides her, silently asking him if he wanted a drink as well. As usual, he declined. 

“He is nice.” Dean agreed, crossing a leg over the other as he laid back in his seat. They were the last ones at the bar. “Maybe Italians are intense like that, I don’t know. We just casually chat sometimes at night when I head back to get some sleep. Whenever I wake up he’s never around. Sometimes I see him around the place, just like everyone else who is staying at the hotel. I’m also staying for free, remember? I wasn’t going to turn it down.” 

“He’s hot.” 

“What?” Dean laughed and raised an eyebrow, as he turned to face Charlie. 

“What!” The woman huffed and crossed her arms under her breasts, giving Dean a glare. “Just because I’m not into men doesn’t mean I can’t acknowledge an attractive one.” 

The musician didn’t share much more of his experience of a week living in Cas’ home. He had his own bathroom, which meant he rarely had to leave his room whenever he was in the house. Plus, the entire building was big enough for the two men to never actually bump into each other. Whenever they did, it was because one was actively seeking for the other. Like that one time Cas cooked dinner for the both of them. Not like Dean ever told Charlie that. Some things were better left a secret. 

Though that night had been Dean’s best night in Tuscany so far. Cas prepared pizza and Dean could’ve sworn he fell in love with him right then. Maybe not in love, but in like for sure. They talked and laughed until they were crying so much their stomachs hurt. Dean didn’t know how to describe the feeling he got whenever he was with Cas. The Italian saw him as a person and not some famous guy that everyone seemed to think they could buy. Cas cared. He looked at him like he understood and it made Dean ache for more. He came clean with everything, just simply let it all out, and Cas _hugged_ him. He didn’t say anything else and they both shared one last drink before heading to bed. 

Dean lied about not seeing him after he woke up. Cas was starting to be the reason why he woke up. He didn’t know when hearing what Cas dreamed about became so important. But he wanted to know all about his fantasies. They were fascinating. Not to mention Cas would always offer to cook and Dean’s palate was always glad about it. Their last breakfast ended in a foodfight, with flour all over Cas’ face and Dean pinning him to the kitchen counter. They definitely stared at each other’s lips but no one was brave enough to make a move. 

\--

During the middle of his second week, Charlie wanted to go horse riding. 

“My high school best friend loved it. He did it professionally, too.” Dean hummed softly. “Equestrian I think was the name? I don’t know. I just remember making a lot of jokes about him and riding.” He chuckled at the memory and smiled fondly to himself. 

“Oh?” Charlie raised an eyebrow, looking over at Dean out of the corner of her eye. “You sure that was the only thing he knew how to ride?” She smirked and put on her sunglasses, as they stepped out of the hotel building. 

“Hey.” Dean scoffed and rolled his eyes, nudging Charlie’s side gently with his elbow. “Get your mind out of the gutter. “Nothing like that ever happened.” 

There was nothing to hide there. Dean was an open book when it came to Benny. They shared their first cigarette together at the age of fourteen and became inseparable ever since. Well, until they actually did. 

Benny was aware of Dean’s desires. He knew that the boy eventually was going to drop out in order to pursue his dreams and he had always been supportive about it. School wasn’t for everyone and if Dean would be happier on the road, playing that shitty acoustic guitar that was always lacking a string, then Benny would be happy as well. He even offered his best friend money. _It’s a starting point_ , he said. He should’ve known better than to expect Dean to accept it. If their places had been reversed, he wouldn’t have taken the money either. 

They simply fell out of touch. Dean knew Benny had big plans with his career, but he was certain that something happened to him. Every day for two years after they lost contact Dean always checked the news with hopes of seeing his name _somewhere_. Maybe he got injured? Or maybe he ended up realizing horse riding really wasn’t his thing? Dean would probably never know the answer to any of his questions. 

“He changed his number, too, apparently.” Dean cleared his throat and rubbed the back of his neck as he looked around, furrowing his eyebrows slightly. He had never seen horses during his entire stay. “Hey, are you sure we can actually go horse riding?” 

“Sure you can. But not here.” 

Dean spun around quickly at the sudden third - yet familiar- voice. He swallowed nervously as he noticed that Cas was standing way closer than what he had been expecting. He stared into the man’s eyes for a moment and licked over his lips gently, as he raised an eyebrow. “How come you always appear out of nowhere?”

“Magic.” Cas said, completely serious. 

The redhead looked back and forth between Dean and Cas, not knowing whether to interrupt whatever was going. She didn’t know what it was, but it was definitely not _nothing_. Which meant that during the past days _something_ had also been happening and Dean hadn’t been telling her. Rude. 

It wasn’t until she cleared her throat that the two men realized she was there as well. The musician quickly took a step back and stood up straight, sliding his hands into the back pocket of his jeans. 

“Are all Italians unaware of the concept of personal space?” Dean said casually, trying his best to shrug the situation off. 

Cas rolled his eyes at that and placed his hands on his hips, staring at the two Americans for a moment. “As I was saying, we don’t offer horse riding. We don’t have horses.” 

“What?” Dean scoffed and crossed his arms over his chest, narrowing his eyes at the blue eyed man. “Last night you showed me them, remember? When we went out for a walk?”

Cas had insisted on how it was too early to go to bed, even though the clock on the wall clearly signaled that it was two in the morning. The Italian gave Dean a private tour of the place and showed him all of his favorite spots, including where they had all of the animals. Cas told Dean where he had his first kiss and how he always came to the same tree whenever he missed his parents, who had died in a car crash. _They got engaged here_ , he said and looked up at the big weeping willow tree. Dean just listened intently to everything Cas had to say, worried that if he talked he would ruin the moment. The more Cas told Dean about his life, the more his heart thumped in his rib cage. By the end of the night, the rockstar’s fingers found their way to Cas’. It was the first time they held hands. 

“You went out for a walk?” Charlie’s eyes widened, lips parting slightly, her brain trying to put together all the new small pieces of information she was getting. “With him?” She pointed a thumb at Cas, who was positively ignoring her. 

“Yes.” Cas agreed and raised an eyebrow at Dean. “I also told you I don’t see horses as means of transportation.” He huffed and crossed his arms over his chest.

“Means of-” Charlie shook her head and stared bewildered at the scene displaying right in front of her. She had never felt so invisible in her life. 

“Oh, come on!” Dean scoffed at that and let out a heavy sigh, even though his eyes held nothing but fondness for the other man. 

“Don’t ‘come on’ me.” Cas narrowed his eyes, unaware of the woman leaving. 

“You’re ridiculous.” 

“Am not.”

“Shut up already.” 

Dean rolled his eyes to himself and pinched the bridge of his nose with his thumb and index finger. There was something warm building up inside his chest and he wasn’t sure if he liked it. It felt weird. Way too weird. He wasn’t used to having such strong… feelings. It made him feel fuzzy and tingly. Cas made him feel fuzzy and tingly and Dean wasn’t fighting any of it.

“Make me.” Cas raised an eyebrow, not sure where he was actually going with such a challenge. It just felt right at the moment. 

Green orbs quickly met blue ones. Dean’s eyes slowly traveled down to Cas’ lips, feeling his throat going dry all of a sudden. He involuntarily licked over his own parted ones and looked away before he could blush. 

“You’re stupid.” 

The loud laugh that ripped through Cas’ body would’ve seemed ugly to many. Dean just thought it was lovely. The Italian’s eyes crinkled with such pure and utter _happiness_ , it was impossible to look away. Cas’ inner light was so bright Dean was attracted to it before he was even aware of it himself.

The musician was only brought back to reality when Cas spoke. Did he speak? He wasn’t quite sure. Dean blinked quickly and shook his head slightly, looking over at the brunette once again. 

“What?” Dean spoke softly, biting at the inside of his cheek. 

“Your friend.” Cas nodded and waved a hand over the empty spot where Charlie previously stood. “She left. Shouldn’t you go after her?” He hummed.

“Oh. Yeah.”

Dean cleared his throat and put on his sunglasses, in hopes of hiding his clearly nervous stare. He didn’t want Cas to think he was the cause of his troubled state (even if he was). He patted Cas’ shoulder as he walked past him, being perfectly aware that he was letting his fingers linger there for longer than necessary. But he wasn’t going to think about that. He also wasn’t going to think about how Cas tilted his head to the side just enough for his lips to graze over his knuckles. Instead, he had to figure out what excuse he was going to try and sell Charlie. Dean just knew that the girl would bombard him with questions about what his true relationship with Cas was. 

Which was exactly what happened. 

Dean texted Cas he would be back home late that night. For some odd reason, a voice deep inside his head told him to let the other know that their midnight conversations would be delayed. He had a particular something to take care of first. Really, it was a particular someone. It’s not like he was looking forward to it, but Dean knew that if he didn’t at least give Charlie the slightest piece of information about what was going, she would never let go of the subject of him and Cas. Him and Cas? Dean and Cas. Cas and Dean. _Castiel_. It sounded nice in his head. 

That’s how Dean found himself lying on Charlie’s bed with some weird cucumber mask on his face. The redhead had insisted that for him to be telling her such intimate things he needed to relax. Although Dean was pretty sure it was an excuse for not having a spa night all by herself. 

“Intimate? It’s not intimate.” Oh it was very intimate. 

Dean scoffed and crossed his arms behind his head, letting out a heavy sigh as he stared at the ceiling. “There’s nothing intimate about it. We just talk.” He murmured. “And yes, we go for walks.” He quickly added as he noticed Charlie’s eyes widening slightly and lips parting. In the almost two weeks they had known each other, Dean had learned to read her pretty quickly. They did spend every day together, after all. Just like how he spent every night with Cas talking about everything and nothing. Dean came to the conclusion he just liked the sound of Cas’ voice. 

“Is that really all there is to it, though?” Charlie narrowed her eyes, searching for her phone. “I feel like you’re not telling me something.”

“We also have dinner, sometimes.” Everynight. 

“Oh?”

“It’s nothing.” Dean shook his head. “Nothing is happening either. And nothing ever will.” 

“You sure?” Charlie raised an eyebrow, as he stared at her phone screen. “Because the Bratz Love Meter says you and Castiel are a real-life Romeo and Juliet.” She hummed and practically shoved her phone on Dean’s face, tapping over the pink thermometer eagerly. “And this shit never lies, I swear.” 

“Have you been seriously taking romantic advice from some doll’s game?” Dean scoffed and grinned widely. Though he was just taking advantage of the situation to tease her instead, as he continued to stare at the game love bar on the screen. What if the thing really never lied? No. Dean had to be very desperate for him to even consider believing that shit. And if there was one thing Dean Winchester absolutely wasn’t, was desperate. _Unless…_

“No. Yes. I don’t know. Maybe? Sometimes.” Charlie huffed and hit Dean’s shoulder gently. 

The conversation soon enough moved to other topics. Mainly because Dean wasn’t letting out any more details of the obvious bond he had been building with the owner of the place over the past weeks.  


\--

By the end of the third week, Charlie left. 

Dean hugged her tightly, for at least five minutes. She had been the first person he had been able to truly call a friend ever since Benny. Sammy could’ve been considered his friend, too, for sure. But having your little brother as your best friend was getting kind of lame. It was weird how Dean had fame and money yet he didn’t really have people by his side. They were usually below him. Or above. Though the older he got, those one night stands started to considerably lose their appeal. 

“Take care of yourself, okay? Don’t be a stranger. You have my number.” Dean reminded her as he finally let go of Charlie. 

“Yeah, yeah. Don’t go sappy on me. Let me know when you’re touring the States again and get me free tickets. Only then I’ll agree to seeing you again. Maybe.” 

Dean made a mental note to absolutely get her tickets. Sam would adore her. He had a pretty good feeling they would get along quite nicely. Not to mention he would also get to tell his brother he had made an actual friend that wasn’t a bottle of whiskey or his package of cigarettes.

A soft sigh left Dean’s lips as he stood by the entrance of the hotel, staring at the door even after Charlie was long gone. He bit at the inside of his cheek and rubbed his eyes tiredly, once he finally snapped out of it. Vacations weren’t eternal, after all. He couldn’t have expected for her to stay in Tuscany forever. Dean himself had a week left at the ethereal place and he was starting to think he should probably stay for a little longer. Escaping reality had been more attractive than what he first thought. 

Hours went by quickly and Dean lost track of time. He spent the rest of the day walking around the land near the hotel, checking out all the usual spots Charlie and him used to love. Except it felt empty. He furrowed his eyebrows to himself and pursed his lips together, hoping with all of his heart the girl wouldn’t disappear from his life for good. 

Dean looked up at the sky as the sun began to fade away for the day. A small smile appeared on his face as he stared up at the stars and shook his head. There was something about celestial bodies that made him feel awfully peaceful. Which was ironic, because how could Dean find peace in the uncertain and unknown? Maybe he would inquire in that question some other day. It seemed like it would make a cool song. 

How was he supposed to entertain himself for the last days he had of vacation? His partner in crime just left the continent. Dean furrowed his eyebrows deeply as he headed back towards Cas’ house, calling it a day since he didn’t know what else to do. His mind quickly began to go through the place and his lips parted, realizing he had never been to the pool. Charlie always changed the excuse of why she didn’t want to go. One day she was allergic to chlorine, the next one she was allergic to children. Whatever the actual reason was, Dean promised her he wouldn’t insist on it anymore. 

“That would be nice.” Dean whispered to himself and stopped walking. He looked over his shoulder towards the pool of the hotel and pursed his lips together. Of course. It was too late already: it had already closed. Tomorrow then. 

Except Dean wasn’t that patient. He knew Cas was out for the day. The Italian told Dean they would have to cancel their dinner plans because he had some business to attend to in Pisa. Which meant the rockstar had the house to himself… and the pool. It was Cas’ private one but it wouldn’t hurt him if he never knew about it. 

With his mind made up, Dean rushed over to the pool he always walked by whenever he went back to his room. It had always caught his eye, yet he never had the courage to ask Cas if he could actually swim in it. 

His hands were acting before he could even tell his brain to move them. Dean was sure he had never stripped so fast before in his life. He shrugged his shirt off as he stared at the large pool in front of him, biting at the inside of his cheek. An odd sense of adrenaline rushed through him in that moment. Probably because his mind was telling him he was doing something prohibited. Although, if he was realistic, Cas would most likely not care at all. A faint memory of Cas offering him to take a dive began to cloud his mind. Dean wasn’t actually sure if that happened or if he was making it up to justify his actions. Either way, clothes continued to drop next to his feet until he was in his underwear. There was no time to get proper swimwear, considering the drowning feeling of getting caught that was engulfing him.

The water was _perfect_. It was, unexpectedly, warm and it sent shivers running up Dean’s spine as he submerged. He stayed there until his throat started aching and the need for oxygen was overwhelming. Dean pushed himself towards the surface and gasped for air, panting softly. He combed his hair back with his fingers and froze as he noticed the pair of extra shoes by the edge of the pool. 

“Oh shit.” Dean whispered and looked up at the man staring down at him. 

“Enjoying yourself?” Cas hummed softly and raised an eyebrow. 

“I thought you wouldn’t be coming home until late.” Dean murmured and swallowed nervously. He bit at the inside of his cheek and flashed the Italian a small smile. “How did your deal go? Signed a contract?” He had no idea what people that worked in the wine industry actually did. But it seemed correct enough to say it out loud and not make a fool of himself. Hopefully. 

“It is late.” 

“Oh.”

A trillion scenarios displayed in Dean’s imagination at that moment. Though none involved what was actually happening. His lips parted as Cas began to unbutton his shirt and stepped out of his shoes. 

“What are you doing?” He asked dumbly, the warmth of the water suddenly disappearing. He felt as if someone had just thrown ten thousands buckets of ice in the pool. 

“Joining you.” Cas said as if it was obvious. And it was, indeed, pretty obvious. Dean was just experimenting momentary stupidity. 

“Right.” Dean nodded and couldn’t help but devour Cas with his eyes, which was what he had been doing for the past weeks. The Italian didn’t need to be standing half naked in front of Dean for him to visually eat him up. He brought his thumb up to his lips and bit down at the pad of it. If the other man noticed, then he made Dean the favour of not commenting on it. 

“Hi.” Cas whispered as he approached Dean, already in the water. 

“Hey.”

Personal space was nonexistent. Cas leaned forward slightly and brushed the tip of his nose against Dean’s, lips parting as he looked over the man’s face. He had been waiting for weeks and damn he had been patient enough. The Italian had been making sure it was Dean that always led the pace between them. He didn’t want to make the first move and freak the other out. Cas had learned enough about Dean’s issues connecting with others. He would hate himself if he did something Dean wasn’t comfortable with. But it was getting harder and harder to control himself with every passing day. The late night talks and the romantic dinners were beginning to drive Cas insane. He knew something was going on. He had told Dean about his family, his previous school studies, his hobbies, everything. They weren’t just mere acquaintances anymore. It was a decent time to try something more, right? 

Cas cupped Dean’s face, thumbs rubbing gently over the American’s cheekbones. He was going to do it. It was time. He licked over his lips and stared into those gorgeous green eyes that made his head spin. 

“Don’t fight it.” Cas whispered, slowly pressing his chest against Dean’s. He could see the panic in the other man’s eyes. “Don’t fight _me_.” He breathed and molded their lips together. 

Time stopped. Fireworks. Butterflies. All that sappy shit Dean usually laughed about whenever someone else described, was exactly what he felt at that moment. He couldn’t help the soft moan that escaped the back of his throat as he kissed Cas back instantly. 

Cas’ lips tasted like, well, wine. Dean didn’t know what he had been expecting but it wasn’t that. He really should’ve seen it coming, though. It was pretty obvious, once he finally got to feel the man’s tongue against his. Cas had been out doing wine-related businesses earlier, which probably involved a lot of actual wine. It seemed logical enough to him. Even though he didn’t know if drinking your own wine while producing it was actually a thing. Wasn’t that what people always said about not getting high on your own drugs if you’re selling, or whatever? Dean had never been involved with drugs to know enough. And why the hell was he thinking about illegal substances when he had Cas’ lips moving against his? He really was stupid sometimes. Sadly, more often than not. 

It took Dean a whole full minute to stop thinking about other random shit (purely out of nerves) and focus on the half naked man pressed against him. Once he finally managed to kiss back, his mind went blank. He stopped thinking for _good_. He was acting on instinct and started listening to his heart instead of his brain. 

When did they get out of the pool? Dean wasn’t sure. If he had actually passed out of bliss he wouldn’t have been surprised. He was only brought back to his senses when he was pinned harshly to a wall. He opened his eyes slowly, those once bright green eyes now a deep shade of jade; they almost looked brown. It was probably the lust clouding them over. Cas noticed. Dean’s eyes didn’t resemble Granny Smiths anymore, right then. 

Dean’s tongue stuck out and quickly ran over his own bitten lower lip, a shiver running down his spine as his eyes met Cas’. Dean couldn’t actually see the state he was in himself. But if it looked anything like the Italian then he probably looked just as wrecked. 

“The floor.” Dean whispered and ran his hands down Cas’ shoulders, his fingertips gently feeling over the hard biceps underneath. He shifted his weight from one foot to another as he rubbed his thighs together, desperate to get some sort of friction where he needed it the most. “We’re getting your floor wet.” He breathed. The two were still soaking wet, in only their underwear, and the puddles they were leaving on the wood certainly would leave stains later. 

“I’ll just buy a new one.” Cas shrugged a shoulder, his arms wrapping securely around Dean’s waist. He pulled him in close to his chest and kissed him roughly, suppressing the smirk that was threatening to appear on his lips as he felt the American shuddering against him. 

“Fuck. That was hot.” Dean breathed into the kiss, hooking an arm around Cas’ neck. His nails dug gently into his shoulder and licked into his mouth hotly. 

“What, money? I didn’t think you were that superficial, _caro_.” Cas purred and began to kiss down Dean’s neck, sucking soft hickeys here and there.

“No.” Dean shook his head and slid his free hand down Cas’ stomach, slipping his hand inside the wet fabric of his underwear. “Power.” He explained and gently wrapped his fingers around Cas’ hardened cock. The weight of it felt delicious against his palm. “Call me that again.” He whimpered, staring straight into a pair of deep ocean eyes. 

Cas smirked at that and bit at the corner of his lower lip harshly, holding back his own sounds as Dean’s hand began to work on him. “ _Caro_ …” He breathed and ran a hand through his lover’s hair, gripping at the ends of it. He pulled Dean’s head back slightly and licked up his neck and over his jaw line. “You have no idea the things you do to me. _Mi fai impazzire, tesoro_.” 

A visible shiver ran up Dean’s spine, causing him to arch his back off the wall and press up close to Cas. “I have no idea what you just said but, _please_ , fuck me before I go insane.” He begged. Dean Winchester was begging. 

The Italian smirked at that, chuckling softly to himself. Guess they both felt the same way. He cupped Dean’s face and kissed him deeply one last time, before guiding him upstairs to his room.  


\--

Their panting died down not long ago. The moonlight was slipping through Cas’ window in a way that only faintly illuminated their bare torsos. The sheets were all messed up and the bottle of lube discarded on the floor was half empty.

“You know.” Dean breathed, not really wanting to break the silence, as a soft sigh escaped his lips. “I get it now.” He whispered and traced gently over the hickeys he left on Cas’ chest and neck. 

“What?” 

“Why people write love songs.” The American whispered and looked up at Cas, giving him a small smile. 

“I thought you hated them.” Cas whispered back, his fingers continuing to trace soft patterns up and down Dean’s spine. “What changed?”

“I met you.” 

Dean shrugged a shoulder and rested his head back on the pillow, eyes slipping shut. Cas’ bed sheets had to be made out of silk, because there was no other way to explain how soft they were. He bit at the inside of his cheek and hugged the man closer. Who would’ve thought that he would end up being so wrapped up with someone? The entire trip was supposed to give him a break to clear his thoughts. Instead he just ended trying to clear his heart. It was about time he opened up to someone, after all. He wasn’t getting any younger. 

“I think you should stay a bit longer.” Cas whispered and scratched at the back of Dean’s head gently. “With me.”

“Hmm. You know what? Maybe I should.” 

Dean hooked a leg around Cas’ hips and used it as leverage to pull himself up. He sat on the Italian’s lower stomach, biting at the inside of his cheek as he rested his hands on the man’s chest. What if it all ended up hurting him in the end, though? They lived in different countries. Dean wasn’t even sure if he had a real home. It would be tough to maintain a long distance relationship; he knew that much by seeing Sam and Jess’ constant fights. Plus, Dean wasn’t sure if he was willing to keep whatever was going on with Cas strictly as a summer fling. But, he figured those were issues they could work out together in the future. 

_Together_. What an odd concept. Dean was willing to learn to like it. 

“Cas?” 

“Hm?” The man yawned tiredly, reaching for his phone on the nightstand to check the time. Almost one in the morning. He looked back at Dean and placed his hands on the musician’s bare thighs. 

“I _want_ to start composing again.” 

And it was genuine. Dean had ranted about how toxic the music industry was to Cas so many times before. He hated to admit it was the only thing he talked about ninety percent of the time, but he couldn’t help it. Dean had been holding so much in for so long, that when he finally found himself being comfortable around someone, he exploded. It was what happened with Charlie, too.

“Yeah? That’s fantastic.” Cas grinned widely and pulled Dean down for a kiss, squeezing at his thighs tightly. “Anything in particular you wanna write about?” 

Dean nodded and ran his tongue slowly over Cas’ lower lip. He bit at the flesh of it carefully, sucking at it gently, before kissing him properly. 

“You.”

**Author's Note:**

> I'm not really familiar with this ship, but it was written with love.


End file.
